Synthesis of Chiral Hydroxyl Phospholanes from D-mannitol and Their Use in Asymmetric Catalytic Reactions

Wenge Li, Zhaoguo Zhang, Dengming Xiao and Xumu Zhang*

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, Email: zhangxmsustc.edu.cn

W. Li, Z. Zhang, D. Xiao, X. Zhang, J. Org. Chem., 2000, 65, 3489-3496.

DOI: 10.1021/jo000066c (free Supporting Information)

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Abstract

Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides. The use of the hydroxyl phospholane system enables hydrogenation of some substrates in water with >99% ee and 100% conversion (e.g., itaconic acid).

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Synthesis of a Novel Chiral Binaphthyl Phospholane and Its Application in the Highly Enantioselective Hydrogenation of Enamides

D. Xiao, Z. Zhang, X. Zhang, Org. Lett., 1999, 1, 1679-1681.

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Key Words

hydrogenation, reduction of α,β-unsaturated compounds, hydrogen, green chemistry

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ID: J42-Y2000